cis-4,5-Didehydro-16-phenoxy-PGE1 compounds

ABSTRACT

The disclosure includes novel compounds which differ from the known prostaglandins PGF 2 α, PGF 2 β, PGE 2 , PGA 2 , and PGB 2  in that the carbon-carbon double bond in the carboxyl-terminated chain of the novel compounds is in the 4,5-position rather than in the 5,6-position, and in that there is a phenoxy or substituted phenoxy group in the other chain of the novel compounds. These novel compounds are useful for a variety of pharmacological purposes, including abortion, labor induction, and reduction of gastric secretion.

The present application is a divisional application of Ser. No. 678,948,filed Apr. 21, 1976, now pending issuance as United States patent.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from Ser. No. 678,948.

I claim:
 1. An optically active compound of the formula: ##STR1## or aracemic form of that compound and the enantiomer thereof; wherein R₁ ishydrogen or alkyl of one to 12 carbon atoms, inclusive, aralkyl of 7 to12 carbon atoms, inclusive, phenyl, or phenyl substituted with one, 2,or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;wherein M₁ is##STR2## wherein R₂ is hydrogen, methyl, or ethyl; wherein Y₁ istrans-CH═CH-- or --CH₂ CH₂ --; wherein R₈ and R₉ are hydrogen or methylbeing the same or different; and wherein T is alkyl of one to 4 carbonatoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR₃, wherein R₃is alkyl of one to 4 carbon atoms, inclusive; and wherein s is zero,one, 2, or 3 with the proviso that not more than two T's are other thanalkyl;including alkanoates of 2 to 8 carbon atoms, inclusive, andpharmacologically acceptable salts thereof when R₁ is hydrogen.
 2. Anoptically active compound according to claim 1, wherein Y₁ istrans-CH═CH--, R₁ is hydrogen, methyl, or ethyl, M₁ is ##STR3## s iszero or one, T when present is chloro, fluoro, or trifluoromethyl, andR₈ and R₉ are methyl and pharmacologically acceptable salts thereof whenR₁ is hydrogen.
 3. An optically active compound according to claim 1,wherein Y₁ is trans-CH═CH--, R₁ is hydrogen, methyl, or ethyl, M₁ is##STR4## wherein R₂ is hydrogen or methyl, s is zero or one, T whenpresent is chloro, fluoro, or trifluoromethyl, and R₈ and R₉ arehydrogen, and pharmacologically acceptable salts thereof when R₁ ishydrogen.
 4. cis-4,5-didehydro-16-phenoxy-17,18,19,20-tetranor-PGE₁, acompound according to claim 3, wherein R₁, R₂, R₈, and R₉ are hydrogen,and s is zero. 5.cis-4,5-didehydro-16-phenoxy-17,18,19,20-tetranor-PGE₁, methyl ester, acompound according to claim 3, wherein R₁ is methyl, R₂, R₈, and R₉ arehydrogen, and s is zero. 6.cis-4,5-didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGE₁, acompound according to claim 3, wherein R₁, R₈, and R₉ are hydrogen, R₂is methyl, and s is zero. 7.cis-4,5-didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGE₁, methylester, a compound according to claim 3, wherein R₁ and R₂ are methyl, R₈and R₉ are hydrogen, and s is zero.